N-Tetradecanoyl-DL-homoserine lactone

SIGMA/10937 - ≥97.0% (HPLC)

Synonym: N-Myristoyl-DL-homoserine lactone

CAS Number: 98206-80-5
Empirical Formula (Hill Notation): C₁₈H₃₃NO₃
Molecular Weight: 311.46
MDL Number: MFCD01862913
Linear Formula: C₁₈H₃₃NO₃
Product Type: Chemical

Catalog Number	PKG Qty.	Price	Quantity


45-10937-25MG	25 mg	$301.00 1/EAAdd To Favorites		Add To Favorites

application(s)	cell analysis
assay	≥97.0% (HPLC)
color	white to slightly yellow
form	powder
InChI	1S/C18H33NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(20)19-16-14-15-22-18(16)21/h16H,2-15H2,1H3,(H,19,20)
InChI key	ZQAYHOXXVBVXPZ-UHFFFAOYSA-N
Quality Level	100
SMILES string	CCCCCCCCCCCCCC(=O)NC1CCOC1=O
storage temp.	2-8°C

Application:	Induces violacein expression in a Chromobacterium violaceum mutant usually not able to produce homoserine lactones.
Biochem/physiol Actions:	N-Tetradecanoyl-DL-homoserine lactone (C14-HSL) is among a group of homoserine lactones that includes; N-Heptanoyl-DL-homoserine lactone (C7HSL), N-octanoyl-homoserine lactone (N-C8-HSL), N-Decanoyl-DL-homoserine lactone (N-C10-HSL), N-Dodecanoyl-DL-homoserine lactone (C12-HSL), N-(3-oxodecanoyl) homoserine-L-lactone (3-oxo-C10 HSL), N-(3-oxododecanoyl)homoserine-L-lactone (3-oxo-C12-HSL), N-(3-Oxotetradecanoyl)-L-homoserine lactone (3-oxo-C14-HSL, N-(3-hydroxydecanoyl)-L-homoserine lactone, and N-(3-hydroxyoctanoyl)-L-homoserine lactone involved in the processes of bacterial quorum sensing. These N-acyl-homoserine lactones are used to study the processes and mechanisms of bacterial quorum sensing.
Biochem/physiol Actions:	N-Tetradecanoyl-DL-homoserine lactone is a member of N-acyl-homoserine lactone family. N-acylhomoserine lactones (AHL) regulate gene expression in gram-negative bacteria, such as Echerichia and Salmonella are involved in quorum sensing, cell to cell communication among bacteria. Some AHLs are potent chemoattractants for human immune cells such as neutrophils.